Round: 25 Ground: Hardcourt indoor
| ITF Germania F14 | 2016/10/12 15:25 | Tobias Simon v Philipp Davydenko | 6-7,6-7 |
| Challenger Mohammedia Qual | 2016/10/02 10:00 | Tobias Simon v Maxime Janvier | 5-7,4-6 |
| Challenger Mohammedia Qual | 2016/10/01 15:10 | Tobias Simon v Andreas Mies | 4-6,7-6,6-2 |
| Challenger Mohammedia Qual | 2016/10/01 11:00 | Danilo Petrovic v Tobias Simon | 6-3,3-6,6-7 |
| ITF Spagna F32 | 2016/09/27 13:15 | Tobias Simon v Alexander Zhurbin | 2-6,2-6 |
| ITF Spagna F31 | 2016/09/21 15:00 | Jaume Munar v Tobias Simon | 6-4,6-4 |
| ITF Italia F27 | 2016/09/01 11:30 | Tobias Simon v Kristijan Mesaros | 3-6,6-7 |
| ITF Italia F27 | 2016/08/31 13:55 | Pol Toledo Bague v Tobias Simon | 3-6,4-6 |
| ITF Germania F15 | 2016/10/17 08:00 | Jan Simon Vrbsky v Tim Ruehl | 5-7,3-6 |
| ITF Germania F15 | 2016/10/15 08:00 | Tim Ruehl v Patrik Hartmeier | 6-4,6-2 |
| ITF Germania F13 | 2016/10/05 09:35 | Tim Ruehl v Christoph Negritu | 4-6,2-6 |
| ITF Germania F15 | 2015/10/06 09:30 | Tim Ruehl v Martins Podzus | 2-6,1-6 |
| ITF Svizzera F1 - Qual. | 2015/03/08 10:00 | Adam Majchrowicz v Tim Ruehl | 1-6,2-6 |
| ITF Svizzera F1 - Qual. | 2015/03/07 08:00 | Gabriel Currlin v Tim Ruehl | 1-6,3-6 |